Methane → (S)-3-Hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester

HRID 356527Notes

Reaction equation

HRID 356527 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[CH:14][CH:13]=1)([OH:9])[CH:6]([CH3:8])[CH3:7].C>[Pd].C1COCC1.CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C@@:5]([OH:9])([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=1)[CH:6]([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 297MethaneHCID 537325303-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid methyl ester

Product 1

HCID 53666244(S)-3-Hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 4 using 3-[2-(4-benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid methyl ester (8.6 g, 24.2 mmol) from Example SSSS. Three grams of 20% Pd over charcoal and THF:MeOH 1:1 (100 mL). The crude compound was recrystallized from hexanes-ethyl acetate to give racemic title compound (m.p. 89°-91° C.). The title compound was obtained by resolution on a semi-preparative Chiralcel OD column eluting with 90% hexanes, 10% isopropanol and 0.1% trifluoroacetic acid. 1H-NMR (CDCl3) δ 0.93 (d, 3H), 0.95 (d, 3H), 1.68-1.85 (m, 2H), 1.93 (m, 1H), 2.53 (dd, 2H), 2.62 (m, 2H), 3.63 (br s, 1H), 3.71 (s, 3H), 4.97 (br s, 1H), 6.73 (d, 2H), 7.03 (d, 2H).

Workup

  1. customThe title compound was prepared
  2. customThe crude compound was recrystallized from hexanes-ethyl acetate

Sources & evidence

ORD record
ord-9e090457041149eebd7777f6d5d1b6b8
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

Loading…